CN100526292C - Method for synthesizing semicarbazide c,p - aldehyde group benzoic acid of derivative of semicarbazide - Google Patents
Method for synthesizing semicarbazide c,p - aldehyde group benzoic acid of derivative of semicarbazide Download PDFInfo
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- CN100526292C CN100526292C CNB2007100225429A CN200710022542A CN100526292C CN 100526292 C CN100526292 C CN 100526292C CN B2007100225429 A CNB2007100225429 A CN B2007100225429A CN 200710022542 A CN200710022542 A CN 200710022542A CN 100526292 C CN100526292 C CN 100526292C
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- terephthalaldehydic acid
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Abstract
This invention discloses a method for synthesizing terephthalaldhydic acid semicarbazone. The method comprises: reacting semicarbazide and terephthalaldhydic acid under stirring, and monitoring the end point with silica gel thin layer chromatography to obtain terephthalaldhydic acid semicarbazone. The obtained terephthalaldhydic acid semicarbazone has such advantages as simple process and high purity (above 99% after post treatment), and can be used as standard in enzymoimmunoassay of semicarbazide.
Description
Technical field
A kind of Furacilin metabolite Urea,amino-the contract synthetic method of terephthalaldehydic acid of derivative Urea,amino-, belong to technical field of biochemical industry.
Background technology
Urea,amino-, English name: semicarbazide (SEM), CAS#363634, structural formula are NH
2NHCONH
2, be itrofurans medicine nitrofural meta-bolites in animal body.The itrofurans medicine can be used for preventing and treating the sterilization of hydrocoles disease and hydrocoles breeding environment; Also can be used for preventing and treating animal and bird intestines and infect, use more extensive.After the itrofurans medicine enters in the animal body, because the very fast decomposition of less stable, form stable compound with form and animal tissues's protein binding of metabolite.Because the strong toxicity of itrofurans medicine and carcinogenic side effect, caused the great attention of countries in the world and banned use of.Because the violation of this illegal drug is used, cause residually in animal body, but domestic detection technique stays in the detection of former medicine more at present, about the detection research of metabolite seldom, what have also is only limited to instrument detecting.Along with the raising of international standard, the internationalization of China's trade, this detection technique can not meet the demands, be necessary research more effective detection method efficiently---Enzyme-multiplied immune technique (ELISA), this just need Urea,amino-derivative.Up to the present, domestic still not at the Furacilin metabolite Urea,amino-the derivative report of enzyme linked immunosorbent detection, in order to remedy this blank, be necessary the derivative of synthesizing amino urea.
Summary of the invention
The purpose of this invention is to provide the contract synthetic method of terephthalaldehydic acid of a kind of Furacilin metabolite semicarbazide derivative Urea,amino-so that Urea,amino-enzyme linked immunosorbent detection, for people's research from now on provides approach easily.
Technical scheme of the present invention: with Urea,amino-is raw material, under agitation with terephthalaldehydic acid reaction, and with silicon thin-layer chromatography monitoring reaction terminal point, the synthesis of derivatives Urea,amino-terephthalaldehydic acid (CPSEM) that contracts.Its reaction equation is:
The Urea,amino-terephthalaldehydic acid Urea,amino-terephthalaldehydic acid that contracts
Processing step is:
(1) synthetic: Urea,amino-and terephthalaldehydic acid are used dissolved in distilled water with Urea,amino-earlier for waiting mole charging capacity, and (0.013～0.027mol) Urea,amino-adds distilled water 10mL dissolving in the beaker that the magnetic agitation apparatus is installed to take by weighing 1～2g; In addition terephthalaldehydic acid is dripped N, dinethylformamide makes dissolving, take by weighing terephthalaldehydic acid 2～4g (0.013～0.027mol), slowly drip N, dinethylformamide (DMF) to terephthalaldehydic acid dissolves fully; Under agitation Urea,amino-solution is added in the terephthalaldehydic acid solution, temperature of reaction is controlled at 20～30 ℃, reacts 2 hours.
(2) reaction end monitoring: silicon thin-layer chromatography (TLC) monitoring, 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ l point in line place, point sample finishes, and dries up, and thin plate is put into the chromatography fluid cylinder, chromatographic solution is methyl alcohol-chloroform mixed solvent, methyl alcohol/chloroform volume ratio 1: 19 is launched chromatography to 5～6cm place, gets plate, dry up solvent, thin plate is placed uv analyzer, observe at the 254nm wavelength, at R
F=0.3～0.32 observes corresponding point, as reaction end.
(3) purify: reacting liquid filtering is obtained white solid, filter then, repeats 2～3 times, filter and expect to put into 30 ℃ of dryings of vacuum drying oven, obtain the derivative Urea,amino-terephthalaldehydic acid that contracts with distilled water wash.
The making of its used silica gel thin layer plate: get silica gel 12g, be dissolved in the sodium cellulose glycolate solution of 40ml0.5% mass concentration, fully stir into pasty state with glass stick, ultra-sonic oscillation 1 minute, be uniformly coated on 3cm * 8cm sheet glass, after the In Shade seasoning, the baking oven of putting into 105 ℃ activates 1 hour, and it is standby to put into loft drier then.
Beneficial effect of the present invention: the present invention successfully synthesize the Furacilin metabolite Urea,amino-the derivative Urea,amino-terephthalaldehydic acid that contracts, synthesis step is succinct, through aftertreatment, purity is up to more than 99%, can be used as standard substance fully, for later people to Urea,amino-enzyme linked immunosorbent detection research approach easily is provided, can satisfy domestic needs to its research.
Description of drawings
The contract high-efficient liquid phase chromatogram of terephthalaldehydic acid of Fig. 1 Urea,amino-.
The contract uv-absorbing figure of terephthalaldehydic acid of Fig. 2 Urea,amino-.
The contract mass spectrum positive ion figure of terephthalaldehydic acid of Fig. 3 Urea,amino-.
The contract mass spectrum negative ion figure of terephthalaldehydic acid of Fig. 4 Urea,amino-.
Embodiment
(1) making of silica gel thin-layer plate:
Get silica gel 12g, be dissolved in the sodium cellulose glycolate solution of 40ml0.5% mass concentration, fully stir into pasty state with glass stick, ultra-sonic oscillation 1 minute, be uniformly coated on 3cm * 8cm sheet glass, after the In Shade seasoning, the baking oven of putting into 105 ℃ activates 1 hour, and it is standby to put into loft drier then.
(2) the derivative Urea,amino-contracts synthesizing of terephthalaldehydic acid (CPSEM):
Take by weighing the Urea,amino-of 1.5g (0.020mol), in the beaker that the magnetic agitation apparatus is installed, add distilled water 10mL, terephthalaldehydic acid 3g (0.020mol), slowly drip N, dinethylformamide (DMF) to terephthalaldehydic acid dissolves fully, add the solution of Urea,amino-1g (0.013mol) in the stirring, the entire reaction temperature is controlled at 20～30 ℃, reacts 2 hours.
Silicon thin-layer chromatography (TLC) monitoring: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ l point in line place, and point sample finishes, and dries up, thin plate is put into the chromatography fluid cylinder, and chromatographic solution is methyl alcohol/chloroform, volume ratio 1: 19, launch chromatography to the 5.5cm place, get plate, dry up solvent.Thin plate is placed uv analyzer, observe at the 254nm wavelength.At R
F=0.3 can be observed corresponding point.
Purify: reacting liquid filtering is obtained white solid, filter then with the 10mL distilled water wash, repeats 3 times, filtration expects to put into 30 ℃ of dryings of vacuum drying oven, obtains the derivative Urea,amino-terephthalaldehydic acid (CPSEM) that contracts.
Claims (1)
- A Urea,amino-the contract synthetic method of terephthalaldehydic acid of derivative Urea,amino-, it is characterized in that with Urea,amino-be raw material, under agitation with the terephthalaldehydic acid reaction, with silicon thin-layer chromatography monitoring reaction terminal point, the synthesizing amino urea terephthalaldehydic acid that contracts, step is:(1) synthetic: Urea,amino-is to wait a mole charging capacity with terephthalaldehydic acid, earlier Urea,amino-is used dissolved in distilled water, in addition terephthalaldehydic acid is dripped N, dinethylformamide makes dissolving, under agitation Urea,amino-solution is added in the terephthalaldehydic acid solution, temperature of reaction is controlled at 20～30 ℃, reacts 2 hours;(2) reaction end monitoring: the silicon thin-layer chromatography monitoring, 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ l point in line place, point sample finishes, and dries up, and thin plate is put into the chromatography fluid cylinder, chromatographic solution is methyl alcohol-chloroform mixed solvent, methyl alcohol/chloroform volume ratio 1:19 launches chromatography to 5～6cm place, gets plate, dry up solvent, thin plate is placed uv analyzer, observe at the 254nm wavelength, at R F=0.3～0.32 observes corresponding point, as reaction end;(3) purify: reacting liquid filtering is obtained white solid, filters then, repeats 2～3 times, filter and expect to put into 30 ℃ of dryings of vacuum drying oven with distilled water wash, obtain Urea,amino-the derivative Urea,amino-terephthalaldehydic acid that contracts.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100225429A CN100526292C (en) | 2007-05-11 | 2007-05-11 | Method for synthesizing semicarbazide c,p - aldehyde group benzoic acid of derivative of semicarbazide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100225429A CN100526292C (en) | 2007-05-11 | 2007-05-11 | Method for synthesizing semicarbazide c,p - aldehyde group benzoic acid of derivative of semicarbazide |
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| CN101050192A CN101050192A (en) | 2007-10-10 |
| CN100526292C true CN100526292C (en) | 2009-08-12 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880711A (en) * | 2014-03-06 | 2014-06-25 | 陕西科技大学 | Method for preparing aldehyde semicarbazone Schiff base |
| CN106093379A (en) * | 2016-06-08 | 2016-11-09 | 中国科学院广州生物医药与健康研究院 | A kind of semicarbazides derivatization reagent and rapid detection card thereof |
| CN106905715B (en) * | 2017-03-01 | 2018-07-24 | 山西大学 | The pigment and preparation method thereof that fades of one organic molecular species modification |
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2007
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Non-Patent Citations (2)
| Title |
|---|
| Preparation of monoclonal antibodies against aderivative of semicarbazide as a metabolic target ofnitrofurazone. Aizhong Gap etal.analytica chimica acta,Vol.592 No.1. 2007 |
| Preparation of monoclonal antibodies against aderivative of semicarbazide as a metabolic target ofnitrofurazone. Aizhong Gap etal.analytica chimica acta,Vol.592 No.1. 2007 * |
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